3-[(2S,4R)-4-(benzoyloxy)-1-methyl-5-oxopyrrolidin-2-yl]-1-[(2S,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-(methoxycarbonyl)oxan-2-yl]-1λ5-pyridin-1-ylium bromide

• ChemBase ID: 160961
• Molecular Formular: C30H33BrN2O12
• Molecular Mass: 693.49322
• Monoisotopic Mass: 692.12168651
• SMILES: c1(c[n+](ccc1)[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)[C@H]1N(C(=O)[C@@H](C1)OC(=O)c1ccccc1)C.[Br-]
• Canonical SMILES: COC(=O)[C@H]1O[C@H]([n+]2cccc(c2)[C@@H]2C[C@H](C(=O)N2C)OC(=O)c2ccccc2)[C@@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C.[Br-]
• InChI: InChI=1S/C30H33N2O12.BrH/c1-16(33)40-23-24(41-17(2)34)26(30(38)39-5)44-28(25(23)42-18(3)35)32-13-9-12-20(15-32)21-14-22(27(36)31(21)4)43-29(37)19-10-7-6-8-11-19;/h6-13,15,21-26,28H,14H2,1-5H3;1H/q+1;/p-1/t21-,22+,23+,24+,25-,26+,28-;/m0./s1
• InChIKey: AFPUKFPHPAWMEP-QQVAJBBCSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2S,4R)-4-(benzoyloxy)-1-methyl-5-oxopyrrolidin-2-yl]-1-[(2S,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-(methoxycarbonyl)oxan-2-yl]-1λ^5-pyridin-1-ylium bromide
• IUPAC Traditional name: 3-[(2S,4R)-4-(benzoyloxy)-1-methyl-5-oxopyrrolidin-2-yl]-1-[(2S,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-(methoxycarbonyl)oxan-2-yl]-1λ^5-pyridin-1-ylium bromide
• Synonyms: (2S-trans)-3-[4-(Benzoyloxy)-1-methyl-5-oxo-2-pyrrolidinyl]-1-(2,3,4-tri-O-acetyl-6-methyl-β-D-glucopyranuronosyl)-pyridinium Bromide; trans-3'-Benzoyloxy Cotinine 2,3,4-Tri-O-acetyl-N-β-D-glucuronide Methyl Ester Bromide

Database IDs

• CAS Number: 146490-58-6
• PubChem SID: 162255096
• PubChem CID: 71313559

CALCULATED PROPERTIES

• Acid pKa: 17.717213
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): -2.8057113
• LogD (pH = 7.4): -2.8057113
• Log P: -2.8057113
• Molar Refractivity: 146.4596 cm^3
• Polarizability: 58.73741 Å^3
• Polar Surface Area: 164.92 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Beige Solid

DETAILS

Toronto Research Chemicals - B208175

Used in the preparation of Cotinine derivatives, metabolites of Nicotine in humans.

REFERENCES

• Byrd, G., et al.: Drug Metab. Dispos., 20, 192 (1992)
• Benowitz, N., et al.: Br. J. Clin. Pharmacol., 51, 53 (1992)
• Hanioka, N., et al.: Xenobiotica, 31, 687 (1992)
• Ethell, B., et al.: Biochem. Pharmacol., 65, 1441 (1992)
• Yamanaka, H., et al.: Eur. J.